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ReactionSmiles

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int64
1
5
N1=CC=CC2=CC=CC(=C12)S(=O)(=O)Cl.COC=1C(=C2C=CNC2=CC1)CN(C)C>>COC=1C(=C2C=CN(C2=CC1)S(=O)(=O)C=1C=CC=C2C=CC=NC12)CN(C)C
5
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([C:18]2[N:19]=[C:20]3[C:26]([C:27]([NH:29][CH:30]([CH3:32])[CH3:31])=[O:28])=[CH:25][N:24](COCC[Si](C)(C)C)[C:21]3=[N:22][CH:23]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(N)CN>ClCCl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([C:18]2[N:19]=[C:20]3[C:26]([C:27]([NH:29][CH:30]([CH3:32])[CH3:31])=[O:28])=[CH:25][NH:24][C:21]3=[N:22][CH:23]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
1
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([CH2:17][C:18]3[O:22][N:21]=[C:20]([CH2:23][CH2:24][CH2:25][CH2:26]OS(C4C=CC(C)=CC=4)(=O)=O)[N:19]=3)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[NH:46]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48]>C(OCC)(=O)C.O.CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([CH2:17][C:18]3[O:22][N:21]=[C:20]([CH2:23][CH2:24][CH2:25][CH2:26][N:46]([C:47]([O:49][C:50]([CH3:51])([CH3:52])[CH3:53])=[O:48])[C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[N:19]=3)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1
2
C1(=CC(=CC=C1)CC(CCC1N(C(CC1)=O)CCCCCCC#N)O)C1=CC=CC=C1>>C1(=CC(=CC=C1)CC(CCC1N(C(CC1)=O)CCCCCCC#N)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1
5
ClC(=O)OC1=CC=CC=C1.CC(N)CC1=CNC2=CC=CC=C12>ClCCl.c1ccncc1>C1(=CC=CC=C1)OC(NC(CC1=CNC2=CC=CC=C12)C)=O
3
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.Br[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1>CN(C)C=O>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)=[N:10][CH:11]=1
2
OC=1C=C(C=CC1)B(O)O.ClC=1N=C(C2=C(N1)N(C=C2)CCN(C)C)N2CCOCC2>O.C([O-])([O-])=O.[Na+].[Na+].COCCOC.c1ccc(cc1)[P](c2ccccc2)(c3ccccc3)[Pd]([P](c4ccccc4)(c5ccccc5)c6ccccc6)([P](c7ccccc7)(c8ccccc8)c9ccccc9)[P](c1ccccc1)(c1ccccc1)c1ccccc1>CN(CCN1C=CC2=C1N=C(N=C2N2CCOCC2)C=2C=C(C=CC2)O)C
3
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH2:24][CH3:25])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.[CH3:26][O:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH2:24][CH3:25])[C:12]2[N:13]=[C:14]([NH:32][C:31]3[CH:33]=[CH:34][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1
1
[C:1]1([CH2:7][S:8]([NH:11][C@H:12]([B:20]([O:22]C23CC(C2(C)C)CCC3(O)C)[OH:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C1(B(O)O)C=CC=CC=1.C1(B(O)O)C=CC=CC=1.C12(O)CC(C1(C)C)CCC2(O)C>CC#N.CCCCCC>[C:1]1([CH2:7][S:8]([NH:11][C@H:12]([B:20]([OH:22])[OH:21])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
1
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]([CH:13]1[CH2:15][CH2:14]1)[C:7]2=[O:16].Cl.[CH3:18][C:19]1([NH2:22])[CH2:21][CH2:20]1.CCN(CC)CC.O>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:22][C:19]1([CH3:18])[CH2:21][CH2:20]1)[N:8]([CH:13]1[CH2:15][CH2:14]1)[C:7]2=[O:16]
1
Cl.[Cl:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][CH2:8][N:9]([CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21][CH3:22])=[O:20])[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[C:35]([N:37]=[C:38]([N:40]1CCNCC1)[S-])#[N:36].O.[NH2:47]N>>[NH2:47][C:38]1[NH:37][C:35]([N:13]2[CH2:14][CH2:15][CH:10]([N:9]([CH2:16][C:17]3[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=3[C:19]([O:21][CH3:22])=[O:20])[CH2:8][CH2:7][C:6]3[CH:27]=[CH:28][C:3]([Cl:2])=[CH:4][CH:5]=3)[CH2:11][CH2:12]2)=[N:36][N:40]=1
1
C(C(=O)C)(=O)OCC.BrC1=C(C=CC=C1)NN>>BrC=1C=CC=C2C=C(NC12)C(=O)OCC
5
FC1=C(C=CC2=C1C(=C(O2)\C(\C(C)C)=N/O)C)F>CCO[H].[Zn].[Cl-].[NH4+]>FC1=C(C=CC2=C1C(=C(O2)C(C(C)C)N)C)F
3
C(C1=CC=CC=C1)(=O)Cl.NC=1SC=C(C1C(=O)OC)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(=O)NC=1SC=C(C1C(=O)OC)C1=CC=C(C=C1)Cl
5
CI.BrC1=C2CC(C(C2=CC(=C1)CC(C)(C)C)=O)C>C1CCCO1.CO[H].[Na+].[BH4-]>COC1C(CC2=C(C=C(C=C12)CC(C)(C)C)Br)C
3
CN(CCCNC)C.ClC1=CC=C(N=N1)C(=O)OCC>C1CCCO1>CN(CCCN(C1=CC=C(N=N1)C(=O)OCC)C)C
3
Cl.ClCCNCCCl>P(=O)(Cl)(Cl)Cl>ClCCN(P(=O)(Cl)Cl)CCCl
3
C([O:8][C:9]1[CH:35]=[CH:34][C:12]([N:13]([CH2:24][CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:11][CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[Si:17]([O:16][CH2:15][CH2:14][N:13]([C:12]1[CH:34]=[CH:35][C:9]([OH:8])=[CH:10][CH:11]=1)[CH2:24][CH2:25][O:26][Si:27]([C:30]([CH3:31])([CH3:32])[CH3:33])([CH3:29])[CH3:28])([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18]
1
CN1CCNCC1.BrC=1C=CC2=C(C=C(O2)C(=O)O)C1>>BrC=1C=CC2=C(C=C(O2)C(=O)N2CCN(CC2)C)C1
5
C(C1=CC=CC=C1)OC1=CC(=C(C(=O)OC)C=C1)C(F)F>CO[H].[HH].[Pd].[OH-].[Pd+2].[OH-].C>FC(C1=C(C(=O)OC)C=CC(=C1)O)F
3
CC=1C=C(C=CC1C)NS(=O)(=O)C=1C=C2CCC(NC2=CC1F)=O>>CN(C1=C(C=C2CCC(NC2=C1)=O)S(=O)(=O)NC1=CC(=C(C=C1)C)C)C
5
C1(=CC=CC=C1)C=O.ClC1=C(N)C=CC=C1>CCO[H]>C1(=CC=CC=C1)C=NC1=C(C=CC=C1)Cl
3
C(C1=CC=CC=C1)(=O)Cl.ClC1=CC=C(C(=O)Cl)C=C1.O1CCOC12CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)CN>C1(=CC=NC=C1)N(C)C.ClCCl.c1ccncc1>ClC1=CC=C(C(=O)NCC2=CC=C(C=C2)S(=O)(=O)N2CCC3(OCCO3)CC2)C=C1
3
C(#N)C=1C=C(C=CC1)C1=NN(C(C=C1)=O)CC=1C=C(C=CC1)C1=NC=C(C=N1)N1CCN(CC1)NC(=O)OC(C)(C)C>>O=C1C=CC(=NN1CC1=CC(=CC=C1)C1=NC=C(C=N1)N1CCNCC1)C=1C=C(C#N)C=CC1
5
CC1=NNC(=C1)C.ClC1=NC=C(C(=O)NC2=CC(=C(C=C2)Cl)C2=NC=CC=C2)C=C1>N(C)(C)C=O.[H-].[Na+]>ClC1=C(C=C(C=C1)NC(C1=CN=C(C=C1)N1N=C(C=C1C)C)=O)C1=NC=CC=C1
3
NC1=C(C=C(C(=O)N)C=C1)OC1=C(C=C(C=C1)F)F>c1ccncc1.CS(=O)(=O)Cl>FC1=C(OC=2C=C(C(=O)N)C=CC2NS(=O)(=O)C)C=CC(=C1)F
3
ClC=1C2=C(N=CN1)C(=CS2)C(=O)NC2=C(C(=CC=C2F)NS(=O)(=O)CCC)F>>FC1=C(C(=CC=C1NS(=O)(=O)CCC)F)NC(=O)C1=CSC2=C1N=CN=C2
5
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][N:10]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25](=[O:27])[CH3:26])[CH2:20][CH2:19]1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].O>CS(C)=O>[CH3:9][N:10]([CH:18]1[CH2:19][CH2:20][N:21]([CH2:24][C:25]2([CH3:2])[CH2:26][O:27]2)[CH2:22][CH2:23]1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15]
1
[CH3:1][N:2]([CH3:6])[CH2:3][C:4]#[CH:5].Br[C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([Cl:17])[CH:16]=1)[C:13](=[O:18])[N:12]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=1)[CH2:11]2.C(Cl)(Cl)Cl.CO>C(NC(C)C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:17][C:15]1[CH:16]=[C:8]([C:5]#[C:4][CH2:3][N:2]([CH3:6])[CH3:1])[CH:9]=[C:10]2[C:14]=1[C:13](=[O:18])[N:12]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=1)[CH2:11]2
1
[Br:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11])=[N:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1.C(N([CH2:29][CH3:30])CC)C.[C:31](Cl)(=[O:33])[CH3:32].[OH2:35]>C(Cl)Cl>[C:31]([O:11][CH2:10][CH:9]([CH2:8][CH2:7][C:5]1[O:6][C:2]([Br:1])=[C:3]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)[N:4]=1)[CH2:12][O:13][C:29](=[O:35])[CH3:30])(=[O:33])[CH3:32]
2
ClCC1(OC1)C>O.C(C)(=O)O.[N-]=[N+]=[N-].[Na+]>N(=[N+]=[N-])CC(CCl)(O)C
3
CN1C(C=2CCCNC2C=C1)=O.ClC=1N=C2C(=NC1N1CCC3(CC1)CC1=CC(=CC=C1[C@H]3NC(OC(C)(C)C)=O)F)N(N=C2I)C2OCCCC2>C1(=CC=CC=C1)C.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C(OC)=CC=C2OC.CNC5=C(C6=C([Pd]OS(C)(=O)=O)C=CC=C6)C=CC=C5>ClC=1N=C2C(=NC1N1CCC3(CC1)CC1=CC(=CC=C1[C@H]3NC(OC(C)(C)C)=O)F)N(N=C2N2CCCC=3C(N(C=CC23)C)=O)C2OCCCC2
3
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])C.N[C@H:11](C(N[C@H](C(O)=O)CCC(=O)N)=O)CC(C)C.N[C@H](C(N[C@H](C(O)=O)CCC(=O)N)=O)CC1CCCCC1>>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:4][CH3:6])[CH3:11]
1
Cl[CH2:2][CH2:3][O:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[N:11][C:12]=2[NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:17]([Cl:29])[CH:16]=2)[NH:7][N:6]=1.[C:30]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)(=[O:32])[CH3:31]>>[C:30]([N:33]1[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][O:4][C:5]2[C:13]3[C:8](=[N:9][CH:10]=[N:11][C:12]=3[NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[C:17]([Cl:29])[CH:16]=3)[NH:7][N:6]=2)[CH2:35][CH2:34]1)(=[O:32])[CH3:31]
1
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:3]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([CH2:26][O:27][Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])[C:23]=1[O:24][CH3:25])[CH:19]=O.C[Si]([C:42]#[N:43])(C)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>ClCCl>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:19]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:8][CH:9]=2)[C:42]#[N:43])[CH:21]=[C:22]([CH2:26][O:27][Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:30])[CH3:31])[C:23]=1[O:24][CH3:25]
1
C1(=CC=CC=C1)N1CCNCC1.OC(CCCCl)C=1C=C2CCC(NC2=CC1)=O>N(C)(C)C=O.CCN(CC)CC.[I-].[Na+].C(O)([O-])=O.[Na+]>OC(CCCN1CCN(CC1)C1=CC=CC=C1)C=1C=C2CCC(NC2=CC1)=O
3
COC(C1=C(C=CC=C1[N+](=O)[O-])CBr)=O>>COC(C1=C(C=CC=C1[N+](=O)[O-])C=O)=O
5
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:32][CH:33]1[CH:40]2[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:42][CH:34]1[CH2:35]3)[CH2:39]2.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:32][CH:33]2[CH:34]3[CH2:42][CH:38]4[CH2:37][CH:36]([CH2:41][CH:40]2[CH2:39]4)[CH2:35]3)=[O:8])=[CH:9][CH:10]=1
1
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[CH:16]=1)[C:9](=[O:14])N(OC)C)([CH3:4])([CH3:3])[CH3:2].[I:24][C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=1>>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[CH:16]=1)[C:9]([C:28]1[CH:29]=[CH:30][C:25]([I:24])=[CH:26][CH:27]=1)=[O:14])([CH3:2])([CH3:3])[CH3:4]
1
[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:21]3[CH2:23][CH2:22]3)[C:14]=2[N+:18]([O-])=O)[C:9]1=[O:24])[CH3:7])(=[O:3])[CH3:2].C(O)C>[Pd]>[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:21]3[CH2:22][CH2:23]3)[C:14]=2[NH2:18])[C:9]1=[O:24])[CH3:7])(=[O:3])[CH3:2]
1
CC1=CC(=NN1)NCCNC1=NNC(=C1)C>Cl>Cl.Cl.CC1=CC(=NN1)NCCNC1=NNC(=C1)C
3
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:12]([CH3:27])[CH:13]=[C:14]([C:16](=[O:26])[C:17](=[O:25])[NH:18][C@H:19]([CH3:24])[C:20](F)(F)F)[CH:15]=2)=[O:10])=[CH:4][C:3]=1[CH3:28].[NH2:29][C@H:30](C)CC#N>>[C:30]([CH2:20][C@H:19]([NH:18][C:17](=[O:25])[C:16]([C:14]1[CH:15]=[C:11]([C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH3:28])[CH:4]=2)=[O:10])[N:12]([CH3:27])[CH:13]=1)=[O:26])[CH3:24])#[N:29]
2
N1C(CCC1)=O>C1(=CC=CC=C1)C.CCN(CC)CC.C(=O)(Cl)Cl>O=C1N(CCC1)C(=O)Cl
3
COC(C1=CN=C(C=C1)NC(C(CC1CCCC1)C1=CC=C(C=C1)C1=CC=CC=C1)=O)=O>>C1(=CC=C(C=C1)C(C(=O)NC1=NC=C(C=C1)CO)CC1CCCC1)C1=CC=CC=C1
5
BrC=1C=C(C=CC1)N1C2=NC=NC=3C=C(C(=C(CC1CI)C32)OC)OC>>BrC=1C=C(C=CC1)N1C2=NC=NC=3C=C(C(=C(C=C1C)C32)OC)OC
5
C(CCC)C1(CS(C2=C(N(C1)C1=CC=CC=C1)C=C(C(=C2)OCCC(=O)OCC)SC)(=O)=O)CC>Cl.O1CCOCC1>C(CCC)C1(CS(C2=C(N(C1)C1=CC=CC=C1)C=C(C(=C2)OCCC(=O)O)SC)(=O)=O)CC
3
[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11]N[C:9]1=[O:13])(=[O:4])=[O:3].O[CH2:15]CN1CCCC1=O>>[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH2:15][C:9]1=[O:13])(=[O:4])=[O:3]
1
ClC1=C(C(=O)Cl)C=CC(=C1)Cl.C(CC)C=1NOC(C1)=O>C(O)([O-])=O.[Na+]>C(CC)C=1N(OC(C1)=O)C(C1=C(C=C(C=C1)Cl)Cl)=O
3
ClC=1C=C(C#N)C=CN1>C1(=CC=CC=C1)C.[Cl-].[NH4+].C[Al](C)C>ClC1=NC=CC(=C1)C(N)=N
3
O=C1[C@]2(C=3C(=NC=CC3)N1)CC1=CC=C(C=C1C2)C(=O)OC>CO[H].[OH-].[Na+]>O=C1[C@]2(C=3C(=NC=CC3)N1)CC1=CC=C(C=C1C2)C(=O)O
3
[Si](C)(C)(C(C)(C)C)OCC[C@@H](C1=CC=CC=C1)N.BrC=1C=C(C=CC1)C1(S(N=C(OC1(C)C)OC)(=O)=O)C>ClCCl>BrC=1C=C(C=CC1)C1(S(N=C(OC1(C)C)N[C@@H](CCO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)(=O)=O)C
3
C(#C)C1=CC=C(C=C1)F>O.C1CCCO1.[B]1OC2=CC=CC=C2O1>C1(=CC=CC=C1)CCC/C=C/B(O)O
3
FC(F)(F)C([O-])=O.[NH2:8][C@H:9]1[C:16](=[O:17])[N:15]2[C@@H:10]1[CH2:11][CH2:12][C:13]([Cl:21])=[C:14]2[C:18]([OH:20])=[O:19].C(=O)(O)[O-].[Na+].[C:27]1([CH2:33][C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>CC(C)=O.O>[C:27]1([CH2:33][C:34]([NH:8][C@H:9]2[C:16](=[O:17])[N:15]3[C@@H:10]2[CH2:11][CH2:12][C:13]([Cl:21])=[C:14]3[C:18]([OH:20])=[O:19])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
1
C1COCCN1.ClC=1N=C2N(C(C1)=O)C[C@](N2)(C(F)(F)F)C>>C[C@@]1(NC=2N(C(C=C(N2)N2CCOCC2)=O)C1)C(F)(F)F
3
C(C)[C@@H]1CN(S(C2=C(O1)C=CC=C2)(=O)=O)CC2=C(C=CC(=C2)B2OC(C(O2)(C)C)(C)C)C.CN1CC2=CC=C(C=C2CC1)/C=C/C(=O)OCC>O.CCN(CC)CC.O1CCOCC1.Cl[Rh].Cl[Rh].C1CC=CCCC=C1.C2CC=CCCC=C2>C(C)[C@@H]1CN(S(C2=C(O1)C=CC=C2)(=O)=O)CC=2C=C(C=CC2C)C(CC(=O)OCC)C=2C=C1CCN(CC1=CC2)C
3
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]([C:17]2[C:21]4[CH2:22][NH:23][CH2:24][CH2:25][C:20]=4[N:19]([CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[N:18]=2)[CH2:12][CH2:11][CH2:10]3)[CH:4]=[N:3]1.Br[C:33]1[S:34][CH:35]=[N:36][N:37]=1.C(O[Na])(C)(C)C.O1CCOCC1>Cl[Pd-3](Cl)(=C1N(C2C(C(CC)CC)=CC=CC=2C(CC)CC)C=CN1C1C(C(CC)CC)=CC=CC=1C(CC)CC)C1C(Cl)=CC=CN=1.C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]([C:17]2[C:21]4[CH2:22][N:23]([C:33]5[S:34][CH:35]=[N:36][N:37]=5)[CH2:24][CH2:25][C:20]=4[N:19]([CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[N:18]=2)[CH2:12][CH2:11][CH2:10]3)[CH:4]=[N:3]1
2
C1(=CC=C(C=C1)C1=C(C=C2C(=N1)C=C(N2COCC[Si](C)(C)C)SCC(=O)O)Cl)C2=CC=CC=C2>>C1(=CC=C(C=C1)C1=C(C=C2C(=N1)C=C(N2CO)SCC(=O)O)Cl)C2=CC=CC=C2
5
ClC=1C=C2C(=NC(=NC2=C(C1C1=C2C(=NNC2=CC=C1C)C=O)F)N1CC(C1)N(C)C)N1C[C@H](N(C[C@@H]1C)C(=O)OC(C)(C)C)C>O.C1CCCO1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>ClC=1C=C2C(=NC(=NC2=C(C1C1=C2C(=NNC2=CC=C1C)CO)F)N1CC(C1)N(C)C)N1C[C@H](N(C[C@@H]1C)C(=O)OC(C)(C)C)C
3
COC(COCCOC1OCCCC1)=O>>OCCOCC(=O)OC
5
C(C)(C)(C)OP(OC(C)(C)C)N(CC)CC.C(C)N(C(OCC1=CC=CC=C1)=O)CCO>C1CCCO1.ClC=1C=C(C(=O)OO)C=CC1.N1N=NN=C1.S([O-])(O)=O.[Na+]>C(C)(C)(C)OP(=O)(OC(C)(C)C)OCCN(C(OCC1=CC=CC=C1)=O)CC
3
C(C)(C)(C)OC(=O)N1C[C@H](CCC1)NC1=NC=C(C(=N1)C1=CNC2=CC(=CC=C12)C#N)OC(F)F>ClCCl.C(=O)(C(F)(F)F)O>FC(OC=1C(=NC(=NC1)N[C@@H]1CNCCC1)C1=CNC2=CC(=CC=C12)C#N)F
3
C=C1CC=2C(C=3N(C1)N=C1C3CN(CC1)C(=O)OC(C)(C)C)=NOC2>O.C1CCCO1.O.O.[O-][Os](=O)(=O)[O-].[K+].[K+].C[N+]1(CCOCC1)[O-]>OC1(CC=2C(C=3N(C1)N=C1C3CN(CC1)C(=O)OC(C)(C)C)=NOC2)CO
3
[OH:1][CH:2]([CH2:44][N:45]1[C:49](=[O:50])[C:48]2([CH2:55][C:54]([CH3:57])([CH3:56])[N:53]([CH2:58][CH2:59][OH:60])[C:52]([CH3:62])([CH3:61])[CH2:51]2)[NH:47][C:46]1=[O:63])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([OH:43])[CH2:23][N:24]3[C:28](=[O:29])[C:27]4([CH2:34][C:33]([CH3:36])([CH3:35])[N:32]([CH2:37][CH2:38][OH:39])[C:31]([CH3:41])([CH3:40])[CH2:30]4)[NH:26][C:25]3=[O:42])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:7][CH:6]=1.C(O[C:68](=[O:70])[CH3:69])(=O)C>>[C:17]([O:1][CH:2]([CH2:44][N:45]1[C:49](=[O:50])[C:48]2([CH2:51][C:52]([CH3:62])([CH3:61])[N:53]([CH2:58][CH2:59][O:60][C:2](=[O:1])[CH3:3])[C:54]([CH3:57])([CH3:56])[CH2:55]2)[N:47]([C:68](=[O:70])[CH3:69])[C:46]1=[O:63])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([O:43][C:5](=[O:4])[CH3:6])[CH2:23][N:24]3[C:28](=[O:29])[C:27]4([CH2:30][C:31]([CH3:40])([CH3:41])[N:32]([CH2:37][CH2:38][O:39][C:38](=[O:39])[CH3:37])[C:33]([CH3:35])([CH3:36])[CH2:34]4)[N:26]([C:28](=[O:29])[CH3:27])[C:25]3=[O:42])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:9][CH:10]=1)(=[O:20])[CH3:16]
1
O=[C:2]1[C:11]2[C:10]3[C:12]([CH2:16][CH2:17][NH:18][C:19](=[O:27])[CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[NH:5][C:4](=[O:28])[CH2:3]1>C(O)(=O)C.[Pd]>[O:28]=[C:4]1[CH2:3][CH2:2][C:11]2[C:10]3[C:12]([CH2:16][CH2:17][NH:18][C:19](=[O:27])[CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[NH:5]1
1
C(CCC)C(N)(CCCC)C(=O)OCC>>NC(CO)(CCCC)CCCC
5
N1C=CC=CC=1.Cl[C:8]([C:10]1[CH:11]=[CH:12][C:13]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16])=[O:9].[CH2:27]([O:34][C:35]1[C:43]2[N:39]([CH:40]=[C:41]([CH3:46])[C:42]=2[O:44][CH3:45])[CH:38]=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl.C(O)C>[CH2:27]([O:34][C:35]1[C:43]2[N:39]([C:40]([C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:14]([CH:19]=3)[C:15]([O:17][CH3:18])=[O:16])=[O:9])=[C:41]([CH3:46])[C:42]=2[O:44][CH3:45])[CH:38]=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
1
O1CCC(CC1)OC1=C(C#N)C=C(C=C1)B1OC(C(O1)(C)C)(C)C.ClC1=NC(=NC=N1)NC1=NN(C=C1)C>>CN1N=C(C=C1)NC1=NC(=NC=N1)C=1C=CC(=C(C#N)C1)OC1CCOCC1
5
C[C@H]1CC(=O)C=C2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4O)C)C>C1=CC=CC=C1.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(CO)O>C1OC2(CC3=CC[C@H]4[C@@H]5CC[C@@H]([C@@]5(C)CC[C@@H]4[C@]3([C@H](C2)C)C)O)OC1
3
ClC=1C=NC=CC1B1OC(C(O1)(C)C)(C)C.BrC1=C(C=C2C(=CN(C2=C1)CC1CCCC1)CCNS(=O)(=O)C1CC1)F>O.O1CCOCC1.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O.P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>ClC=1C=NC=CC1C1=C(C=C2C(=CN(C2=C1)CC1CCCC1)CCNS(=O)(=O)C1CC1)F
3
[CH3:1][O:2][C@@H:3]1[C@@H:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@@H:8]([CH2:29][O:30]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:7][C@H:4]1[O:5][CH3:6].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C@@H:3]1[C@@H:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@@H:8]([CH2:29][OH:30])[O:7][C@H:4]1[O:5][CH3:6]
1
BrCC(=O)OC(C)C.CC1=C(C=C(C=C1C)C1=CC=CC=C1)CNC=1C(=C(C=CC1F)O)F>CC(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CC1=C(C=C(C=C1C)C1=CC=CC=C1)CNC=1C(=C(OCC(=O)OC(C)C)C=CC1F)F
3
FC=1C=C(C=CC1)B(O)O.C(C)OC(CCCOC1=C(C(=CC=C1)CCCCCCOC1=CC(=CC(=C1)Br)OCC1=CC=CC=C1)CCC(=O)OCC)=O>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2]>C(C)OC(CCCOC1=C(C(=CC=C1)CCCCCCOC=1C=C(C=C(C1)OCC1=CC=CC=C1)C1=CC(=CC=C1)F)CCC(=O)OCC)=O
3
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[C:7]([OH:9])[CH:8]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[O:24][CH2:23][CH2:22][O:21]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:21]1[CH2:22][CH2:23][O:24][CH:20]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:9][C:7]1[CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=[CH:5][C:6]=1[CH3:10]
1
[H+].[B-](F)(F)(F)F.O=O.[Br:9]/[C:10](=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])/[C:11]([OH:13])=[O:12]>CO>[Br:9][C@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:11]([OH:13])=[O:12]
1
OC1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OCC1=CC=CC=C1>CO[H].O.C1(=CC=C(C=C1)S(=O)(=O)O)C>COC1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OCC1=CC=CC=C1
3
FC=1C=C(C(N)=NO)C=CC1C.C(C)(C)(C)OC(=O)N1CCC(CC1)C1=CC(NC=2N1N=CC2C(=O)O)=O>N(C)(C)C=O.C(=O)(C=1NC=CN1)C=1NC=CN1.C(C)(C)N(C(C)C)CC.C1CCC2=NCCCN2CC1>FC=1C=C(C=CC1C)C1=NOC(=N1)C=1C=NN2C1NC(C=C2C2CCN(CC2)C(=O)OC(C)(C)C)=O
3
C(C1=CC=CC=C1)OC1=CC=C(C=C1)SC1=C(C=C(C=C1)[N+](=O)[O-])NC=1C2=C(N=CN1)N=C(C=C2)C>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)SC1=C(C=C(C=C1)N)NC=1C2=C(N=CN1)N=C(C=C2)C
5
C(#N)CC#N.[H-].[Na+].Br[C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15](Br)=[CH:16][CH:17]=3)[C:12](C)(C)[C:11]=2[SiH:10]=1.BrBr.O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[SiH:10]1[C:11]2[CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]=2[CH:20]=[CH:21][CH:9]=1
1
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[N:21][C:22]#[N:23])SC)=[CH:13][CH:12]=1)#[N:10]>O.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[C:22]([N:21]=[C:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]#[N:10])=[CH:12][CH:13]=1)[NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])#[N:23]
1
[CH:1]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1(=O)CCCCC1>[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:9]=[CH:10][C:11]([OH:13])=[O:12]
1
C(C)(=O)NCC(=O)O.ICCC[Si](OCC)(OCC)OCC>CCO[H]>C(C)(=O)NCC(=O)CCC[Si](OCC)(OCC)OCC
3
ClC1=CC=C(CBr)C=C1.C(C(C)C)NS(=O)(=O)C1=CC=C(C=C1)OC>[H-].[Na+].CN(C(C)=O)C>ClC1=CC=C(CN(S(=O)(=O)C2=CC=C(C=C2)OC)CC(C)C)C=C1
3
II.Cl[CH2:4][CH:5]1[CH2:7][CH2:6]1.[Cl:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([C:22]3[CH:23]=[N:24][CH:25]=[N:26][CH:27]=3)=[O:21])=[N:18][CH:19]=2)=[CH:11][CH:10]=1>C1COCC1>[Cl:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([C:22]3[CH:27]=[N:26][CH:25]=[N:24][CH:23]=3)([OH:21])[CH2:7][CH2:6][CH:5]=[CH2:4])=[N:18][CH:19]=2)=[CH:11][CH:10]=1
2
ClC=1C=C(CN)C=CC1.COC(C(=O)O)OC>N(C)(C)C=O.CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1N=CC=C2)OC(=[N+](C)C)N(C)C>ClC=1C=C(CNC(C(OC)OC)=O)C=CC1
3
[CH3:1][C:2]([CH3:56])([CH2:10][C:11]([O:13][C@H:14]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@@H:16]([CH2:17][CH2:18][C@:19]3([CH3:53])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:52])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42]([NH:44][C:45]4[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=4)=[O:43])[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:55])[CH3:54])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].[C:57]([OH:63])([C:59]([F:62])([F:61])[F:60])=[O:58].CC#N>ClCCl>[C:57]([OH:63])([C:59]([F:62])([F:61])[F:60])=[O:58].[OH2:4].[Cl:51][C:48]1[CH:49]=[CH:50][C:45]([NH:44][C:42](=[O:43])/[CH:41]=[CH:40]/[C@:23]23[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:38])[CH3:39])=[C:24]2[C@@H:25]2[C@@:20]([CH3:52])([CH2:21][CH2:22]3)[C@@:19]3([CH3:53])[C@@H:28]([C@:29]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:54])([CH3:55])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:56])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]4)[CH2:27][CH2:26]2)=[CH:46][CH:47]=1
1
C(N(CC)CC)C.[OH:8][CH:9]([C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:10].[CH3:20][S:21](Cl)(=[O:23])=[O:22].[Cl-].[Na+]>C(Cl)Cl>[CH3:20][S:21]([O:8][CH:9]([C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:10])(=[O:23])=[O:22]
1
[CH3:1][P:2]1(=[O:35])[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([NH:15][C:16]3[CH:21]=[C:20]([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=[CH:18][C:17]=3[NH:27]C(=O)OC(C)(C)C)=[O:14])=[CH:9][CH:8]=2)[O:3]1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:27][C:17]1[CH:18]=[CH:19][C:20]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[CH:21][C:16]=1[NH:15][C:13](=[O:14])[C:10]1[CH:11]=[CH:12][C:7]([CH:4]2[O:3][P:2]([CH3:1])(=[O:35])[CH2:6][CH2:5]2)=[CH:8][CH:9]=1
1
CN1N=CC=C1C(=O)Cl.FC(C1=C(C=CC=C1)C1=NC2=C(N1)C=C(C=C2)N)(F)F>ClCCl.CCN(CC)CC>CN1N=CC=C1C(=O)NC=1C=CC2=C(NC(=N2)C2=C(C=CC=C2)C(F)(F)F)C1
3
ClC1=CC(=C2C(=N1)C=CS2)Cl.Cl.FC1=CC=C(C=C1)C(N1[C@@H](CN[C@H](C1)C)C)C1=CC=C(C=C1)F>C(C)(C)N(C(C)C)CC.CC(CC)O>FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C2C(=NC(=C1)Cl)C=CS2)C)C2=CC=C(C=C2)F
3
C(C=C)OC(=O)C1=C(C=CC2=C1C(=C(O2)C)C(=O)Cl)OC2=NC(=CC(=N2)OC)OC>O.ClCCl.CNC>COC1=NC(=NC(=C1)OC)OC1=CC=C2C(C(=C(O2)C)C(N(C)C)=O)=C1C(=O)OCC=C
3
C1(CC1)C(=O)N.ClC1=NC=CC(=C1)OC=1C=C(C2=CC=CC=C2C1)C(=O)OC>O1CCOCC1.[Pd].[Pd].O=C(\C=C\c1ccccc1)\C=C\c2ccccc2.O=C(\C=C\c1ccccc1)\C=C\c2ccccc2.O=C(\C=C\c1ccccc1)\C=C\c2ccccc2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(CC1)C(=O)NC1=NC=CC(=C1)OC=1C=C(C2=CC=CC=C2C1)C(=O)OC
3
[CH2:1]=[C:2]([CH:5]([CH3:11])[CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:3]=[O:4]>[Pd]>[CH3:1][CH:2]([CH:5]([CH3:11])[CH2:6][C:7]([CH3:8])([CH3:10])[CH3:9])[CH:3]=[O:4]
1
C[C@@H]1N[C@@H](CCC1)C.NC=1C2=C(N=C(N1)C=1SC(=CC1)C(C)(C)C)SC(=C2)C=O>>C(C)(C)(C)C1=CC=C(S1)C=1N=C(C2=C(N1)SC(=C2)CN2C(CCCC2C)C)N
5
[OH:1][C@H:2]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:29]=1)[CH2:3][NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]([CH2:22][C:23]([O:25]CC)=[O:24])[N:20]=[N:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+]>>[OH:1][C@H:2]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([NH:35][S:36]([CH3:39])(=[O:37])=[O:38])[CH:29]=1)[CH2:3][NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[N:21]([CH2:22][C:23]([OH:25])=[O:24])[N:20]=[N:19][N:18]=3)=[CH:15][CH:16]=2)[CH2:7][CH2:6]1
1
C(C(C)C)C1N(C(CC(C1)=O)=O)C(=O)OC(C)(C)C>Cl.O1CCOCC1>C(C(C)C)C1CC(CC(N1)=O)=O
3
O=C(C(=O)OC)CCC(=O)OC>O.CO[H].Cl.C1(=CC=CC=C1)NN>C1(=CC=CC=C1)N\N=C(/C(=O)OC)\CCC(=O)OC
3
[P:1](=[O:5])([OH:4])([OH:3])[OH:2].[O-2:6].[Cr+4:7].[O-2:8].[OH2:9]>>[Cr:7]([OH:2])([OH:9])(=[O:8])=[O:6].[P:1](=[O:2])([OH:5])([OH:4])[OH:3]
2
Cl.C1(CC1)C=1C(=CC(=C(C(=O)OC)C1)F)OCC1CCNCC1.BrCC1=C(C(=CC(=C1)Cl)Cl)I>>C1(CC1)C=1C(=CC(=C(C(=O)OC)C1)F)OCC1CCN(CC1)CC1=C(C(=CC(=C1)Cl)Cl)I
5
OC(C)(C)C1=CC=C2C=3C(=CC=C(C3NC2=C1)C(=O)N)B1OC(C(O1)(C)C)(C)C.BrC=1C(=C(C=CC1)N1C(N2C(=CC1=O)C=CC(=C2)OC)=O)C>>OC(C)(C)C1=CC=C2C=3C(=CC=C(C3NC2=C1)C(=O)N)C1=C(C(=CC=C1)N1C(N2C(=CC1=O)C=CC(=C2)OC)=O)C
5
FC(F)(F)C(O)=O.[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[NH:15][C:16]([NH2:25])=[C:17]3[C:21]([N:22]=2)=[N:20][C:19]([O:23][CH3:24])=[N:18]3)[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:37][CH:38]1[CH2:42][CH2:41][O:40][CH2:39]1)(=O)=O.ClC1N=C2C(N=CN2CC2CCOCC2)=C(Cl)N=1>CN(C)C=O.C(OCC)(=O)C>[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([O:23][CH3:24])[N:20]3[CH2:37][CH:38]3[CH2:42][CH2:41][O:40][CH2:39]3)=[C:16]([NH2:25])[N:15]=2)[CH2:10][CH2:9]1
1
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Reaction SMILES Dataset

A collated dataset of 3.4M unique chemical reaction SMILES strings compiled from multiple public sources for use in pre-training and fine-tuning chemical language models.

Reaction SMILES (Simplified Molecular Input Line Entry System) extend the standard SMILES notation to represent complete chemical reactions. They encode reactants, reagents/catalysts, and products in a single text string using the > delimiter:

reactants>reagents>products

For example: CC(=O)O.CCO>[H+]>CC(=O)OCC.O represents the esterification of acetic acid with ethanol to form ethyl acetate.

Dataset Features

  • smiles: The reaction SMILES string
  • source_id: Original data source identifier

Data Sources

Source ID Source URL
1 US Patents 1976-Sep2016 Grants
2 US Patents 2001-Sep2016 Applications
3 CRD 1.37M Dataset (2024)
4 USPTO Year 2023
5 Reaction SMILES Dataset (2023)

License

This dataset aggregates publicly available reaction data. Please refer to the individual source links for specific licensing terms.

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Number of rows:
3,440,704